Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
9-Me-HyperBTM ![]() |
dichloromethane | N Param.: 14.76 sN Param.: 0.67 |
ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434 |
|
7-PivO-HyperBTM ![]() |
dichloromethane | N Param.: 14.49 sN Param.: 0.66 |
ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434 |
|
7-Ms-HyperBTM ![]() |
dichloromethane | N Param.: 12.52 sN Param.: 0.75 |
ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434 |
|
HyperNTM ![]() |
dichloromethane | N Param.: 14.47 sN Param.: 0.72 |
ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434 |
|
HyperPTM ![]() |
dichloromethane | N Param.: 13.43 sN Param.: 0.79 |
ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434 |
|
1,3-bis(trimethylsilyl)propane ![]() |
dichloromethane/MeCN mix | N Param.: -5.30 sN Param.: 1.10 |
Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
|
(4,4-dimethylpentyl)trimethylstannane ![]() |
dichloromethane/MeCN mix | N Param.: -3.90 sN Param.: 1.10 |
Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
|
4-(dimethylamino)pyridine (in DMF) ![]() |
DMF | N Param.: 14.90 sN Param.: 0.67 |
Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
|
p-nitrophenolate (in DMF) ![]() |
DMF | N Param.: 15.05 sN Param.: 0.80 |
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
|
o-nitrophenolate (in DMF) ![]() |
DMF | N Param.: 16.65 sN Param.: 0.70 |
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
|
m-nitrophenolate (in DMF) ![]() |
DMF | N Param.: 22.41 sN Param.: 0.54 |
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
|
p-cyanophenolate (in DMF) ![]() |
DMF | N Param.: 17.85 sN Param.: 0.71 |
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
|
o-(trifluoromethyl)phenolate (in DMF) ![]() |
DMF | N Param.: 20.37 sN Param.: 0.58 |
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
|
p-(trifluoromethyl)phenolate (in DMF) ![]() |
DMF | N Param.: 22.05 sN Param.: 0.53 |
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
|
m-(trifluoromethyl)phenolate (in DMF) ![]() |
DMF | N Param.: 23.40 sN Param.: 0.51 |
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
|
p-chlorophenolate (in DMF) ![]() |
DMF | N Param.: 19.67 sN Param.: 0.72 |
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
|
phenolate (in DMF) ![]() |
DMF | N Param.: 18.86 sN Param.: 0.89 |
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
|
p-methylphenolate (in DMF) ![]() |
DMF | N Param.: 19.65 sN Param.: 0.85 |
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
|
p-(tert-butyl)phenolate (in DMF) ![]() |
DMF | N Param.: 19.90 sN Param.: 0.80 |
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
|
p-methoxyphenolate (in DMF) ![]() |
DMF | N Param.: 19.90 sN Param.: 0.82 |
J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
|
anion of nitroethane (in DMF) ![]() |
DMF | N Param.: 22.21 sN Param.: 0.48 |
Chem. Eur. J. 2008, 14, 6108-6118 10.1002/chem.200800329 |
|
chloro(phenylsulfonyl)methanide (in DMF) ![]() |
DMF | N Param.: 26.64 sN Param.: 0.64 |
Chem. Eur. J. 2008, 14, 6108-6118 10.1002/chem.200800329 |
|
2,2,2-trifluoroethylamine (in DMSO) ![]() |
DMSO | N Param.: 12.15 sN Param.: 0.65 |
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
ethyl glycinate (in DMSO) ![]() |
DMSO | N Param.: 14.30 sN Param.: 0.67 |
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
n-propylamine (in DMSO) ![]() |
DMSO | N Param.: 15.70 sN Param.: 0.64 |
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
morpholine (in DMSO) ![]() |
DMSO | N Param.: 16.96 sN Param.: 0.67 |
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
piperidine (in DMSO) ![]() |
DMSO | N Param.: 17.19 sN Param.: 0.71 |
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
anion of Meldrums acid (in DMSO) ![]() |
DMSO | N Param.: 13.91 sN Param.: 0.86 |
Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] |
|
anion of dimedone (in DMSO) ![]() |
DMSO | N Param.: 16.27 sN Param.: 0.77 |
Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] |
|
anion of acetylacetone (in DMSO) ![]() |
DMSO | N Param.: 17.64 sN Param.: 0.73 |
Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] |
|
anion of ethyl acetylacetate (in DMSO) ![]() |
DMSO | N Param.: 18.82 sN Param.: 0.69 |
Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] |
|
anion of malononitrile (in DMSO) ![]() |
DMSO | N Param.: 19.36 sN Param.: 0.67 |
Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] |
|
anion of ethyl cyanoacetate (in DMSO) ![]() |
DMSO | N Param.: 19.62 sN Param.: 0.67 |
Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] |
|
anion of diethyl malonate (in DMSO) ![]() |
DMSO | N Param.: 20.22 sN Param.: 0.65 |
Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] |
|
anion of nitroethane (in DMSO) ![]() |
DMSO | N Param.: 21.54 sN Param.: 0.62 |
J. Org. Chem. 2003, 68, 6880-6886 10.1021/jo0344182 |
|
anion of diethyl methylmalonate (in DMSO) ![]() |
DMSO | N Param.: 21.13 sN Param.: 0.68 |
J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
|
anion of 3-methyl acetylacetone (in DMSO) ![]() |
DMSO | N Param.: 18.38 sN Param.: 0.72 |
J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
|
anion of nitromethane (in DMSO) ![]() |
DMSO | N Param.: 20.71 sN Param.: 0.60 |
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
|
anion of 2-nitropropane (in DMSO) ![]() |
DMSO | N Param.: 20.61 sN Param.: 0.69 |
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
|
anion of phenylnitromethane (in DMSO) ![]() |
DMSO | N Param.: 18.29 sN Param.: 0.71 |
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
|
anion of p-tolylnitromethane (in DMSO) ![]() |
DMSO | N Param.: 18.31 sN Param.: 0.76 |
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
|
anion of (4-nitrophenyl)nitromethane (in DMSO) ![]() |
DMSO | N Param.: 16.29 sN Param.: 0.75 |
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
|
anion of (3-nitrophenyl)nitromethane (in DMSO) ![]() |
DMSO | N Param.: 18.06 sN Param.: 0.71 |
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
|
anion of (4-cyanophenyl)nitromethane (in DMSO) ![]() |
DMSO | N Param.: 16.96 sN Param.: 0.73 |
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
|
azide ion (in DMSO) ![]() |
DMSO | N Param.: 20.50 sN Param.: 0.59 |
J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
|
4-(dimethylamino)pyridine (in DMSO) ![]() |
DMSO | N Param.: 14.80 sN Param.: 0.67 |
Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
|
anion of 4-nitrobenzyl trifluoromethyl sulfone (in DMSO) ![]() |
DMSO | N Param.: 14.49 sN Param.: 0.86 |
J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b |
|
anion of 4-cyanobenzyl trifluoromethyl sulfone (in DMSO) ![]() |
DMSO | N Param.: 16.28 sN Param.: 0.75 |
J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b |
|
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in DMSO) ![]() |
DMSO | N Param.: 17.33 sN Param.: 0.74 |
J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b |
|
anion of benzyl trifluoromethyl sulfone (in DMSO) ![]() |
DMSO | N Param.: 18.67 sN Param.: 0.68 |
J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b |
|
anion of 4-methylbenzyl trifluoromethyl sulfone (in DMSO) ![]() |
DMSO | N Param.: 19.35 sN Param.: 0.67 |
J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b |
|
bis(4-nitrophenyl)methanide (in DMSO) ![]() |
DMSO | N Param.: 19.92 sN Param.: 0.67 |
ARKIVOC 2008, (x), 37-53 10.3998/ark.5550190.[...] |
|
anion of (4-NO2-C6H4)CH2SO2Ph (in DMSO) ![]() |
DMSO | N Param.: 18.50 sN Param.: 0.75 |
Org. Biomol. Chem. 2008, 6, 3052-3058 10.1039/b805604h |
|
anion of (4-CN-C6H4)CH2SO2Ph (in DMSO) ![]() |
DMSO | N Param.: 22.60 sN Param.: 0.57 |
Org. Biomol. Chem. 2008, 6, 3052-3058 10.1039/b805604h |
|
anion of (4-CF3-C6H4)CH2SO2Ph (in DMSO) ![]() |
DMSO | N Param.: 24.30 sN Param.: 0.51 |
Org. Biomol. Chem. 2008, 6, 3052-3058 10.1039/b805604h |
|
anion of 4-(trifluoromethyl)benzyl-CN (in DMSO) ![]() |
DMSO | N Param.: 27.28 sN Param.: 0.50 |
J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
|
anion of 4-cyanobenzyl-CN (in DMSO) ![]() |
DMSO | N Param.: 25.11 sN Param.: 0.54 |
J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
|
anion of 4-nitrobenzyl-CN (in DMSO) ![]() |
DMSO | N Param.: 19.67 sN Param.: 0.68 |
J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
|
anion of 2-phenyl-propionitrile (in DMSO) ![]() |
DMSO | N Param.: 28.95 sN Param.: 0.58 |
J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
|
anion of 2-(4-CN-C6H4)propionitrile (in DMSO) ![]() |
DMSO | N Param.: 25.35 sN Param.: 0.56 |
J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
|
anion of 2-(4-NO2-C6H4)propionitrile (in DMSO) ![]() |
DMSO | N Param.: 19.61 sN Param.: 0.60 |
J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
|
NaBH4 (in DMSO) ![]() |
DMSO | N Param.: 14.74 sN Param.: 0.81 |
Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 |
|
KBH4 (in DMSO) ![]() |
DMSO | N Param.: 15.14 sN Param.: 0.77 |
Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 |
|
Bu4NBH4 (in DMSO) ![]() |
DMSO | N Param.: 14.94 sN Param.: 0.79 |
Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 |
|
NaB(OAc)3H (in DMSO) ![]() |
DMSO | N Param.: 14.45 sN Param.: 0.76 |
Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 |
|
NaBH3(CN) (in DMSO) ![]() |
DMSO | N Param.: 11.52 sN Param.: 0.67 |
Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 |
|
Ph3P=CH-CO2Et (in DMSO) ![]() |
DMSO | N Param.: 12.21 sN Param.: 0.62 |
J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 |
|
(EtO)2P(O)CH(-)CO2Et (in DMSO) ![]() |
DMSO | N Param.: 19.23 sN Param.: 0.65 |
J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 |
|
(EtO)2P(O)CH(-)CN (in DMSO) ![]() |
DMSO | N Param.: 18.57 sN Param.: 0.66 |
J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 |
|
Ph2P(O)CH(-)CO2Et (in DMSO) ![]() |
DMSO | N Param.: 19.20 sN Param.: 0.69 |
J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 |
|
Ph2P(O)CH(-)CN (in DMSO) ![]() |
DMSO | N Param.: 18.69 sN Param.: 0.72 |
J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 |
|
2-aminobutan-1-ol (in DMSO) ![]() |
DMSO | N Param.: 14.39 sN Param.: 0.67 |
J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
|
benzylamine (in DMSO) ![]() |
DMSO | N Param.: 15.28 sN Param.: 0.65 |
J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
|
1-aminopropan-2-ol (in DMSO) ![]() |
DMSO | N Param.: 15.47 sN Param.: 0.65 |
J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
|
diethanolamine (in DMSO) ![]() |
DMSO | N Param.: 15.51 sN Param.: 0.70 |
J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
|
ethanolamine (in DMSO) ![]() |
DMSO | N Param.: 16.07 sN Param.: 0.61 |
J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
|
imidazole (in DMSO) ![]() |
DMSO | N Param.: 11.58 sN Param.: 0.79 |
Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
|
benzimidazole (in DMSO) ![]() |
DMSO | N Param.: 10.50 sN Param.: 0.79 |
Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
|
2-methyl-benzimidazole (in DMSO) ![]() |
DMSO | N Param.: 10.02 sN Param.: 0.85 |
Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
|
5-methyl-benzimidazole (in DMSO) ![]() |
DMSO | N Param.: 10.69 sN Param.: 0.79 |
Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
|
2,5-dimethyl-benzimidazole (in DMSO) ![]() |
DMSO | N Param.: 10.21 sN Param.: 0.85 |
Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
|
5,6-dimethyl-benzimidazole (in DMSO) ![]() |
DMSO | N Param.: 11.08 sN Param.: 0.71 |
Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
|
5-methoxy-benzimidazole (in DMSO) ![]() |
DMSO | N Param.: 11.00 sN Param.: 0.71 |
Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
|
phenylsulfinate (in DMSO) ![]() |
DMSO | N Param.: 19.60 sN Param.: 0.60 |
J. Am. Chem. Soc. 2010, 132, 4796-4805 10.1021/ja9102056 |
|
phthalimide anion (in DMSO) ![]() |
DMSO | N Param.: 15.52 sN Param.: 0.67 |
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
|
succinimide anion (in DMSO) ![]() |
DMSO | N Param.: 16.03 sN Param.: 0.66 |
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
|
maleimide anion (in DMSO) ![]() |
DMSO | N Param.: 14.87 sN Param.: 0.76 |
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
|
trifluoroacetamide anion (in DMSO) ![]() |
DMSO | N Param.: 15.81 sN Param.: 0.64 |
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
|
N-methyl-trifluoroacetamide anion (in DMSO) ![]() |
DMSO | N Param.: 15.70 sN Param.: 0.71 |
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
|
4,4-dimethyl-glutarimide anion (in DMSO) ![]() |
DMSO | N Param.: 17.52 sN Param.: 0.63 |
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
|
diacetamide anion (in DMSO) ![]() |
DMSO | N Param.: 16.05 sN Param.: 0.70 |
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
|
cyanamide anion (in DMSO) ![]() |
DMSO | N Param.: 20.33 sN Param.: 0.64 |
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
|
p-toluenesulfonamide anion (in DMSO) ![]() |
DMSO | N Param.: 17.14 sN Param.: 0.60 |
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
|
methanesulfonamide anion (in DMSO) ![]() |
DMSO | N Param.: 18.61 sN Param.: 0.53 |
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
|
hydantoin anion (in DMSO) ![]() |
DMSO | N Param.: 17.52 sN Param.: 0.55 |
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
|
1,3-oxazolidin-2-one anion (in DMSO) ![]() |
DMSO | N Param.: 22.40 sN Param.: 0.59 |
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
|
(S)-4-benzyl-1,3-oxazolidin-2-one anion (in DMSO) ![]() |
DMSO | N Param.: 22.67 sN Param.: 0.54 |
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
|
ethyl N-acetylcarbamate anion (in DMSO) ![]() |
DMSO | N Param.: 15.99 sN Param.: 0.70 |
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
|
Me2S=CH-CO2Et (in DMSO) ![]() |
DMSO | N Param.: 15.85 sN Param.: 0.61 |
Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455 |
|
Me2S=CH-CN (in DMSO) ![]() |
DMSO | N Param.: 16.23 sN Param.: 0.60 |
Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455 |

